LIPOPHILIC ANALOGS OF N-ACETYL-NORMURAMOYL-L-ALPHA-AMINOBUTANOYL-D-ISOGLUTAMINE EXHIBITING IMMUNOSTIMULATING ACTIVITY

摘要

In the present invention, there is disclosed a lipophilic analog of N-acetyl-normuramoyl-L-{alpha}-aminobutanoyl-D-isoglutamine exhibiting immunostimulating activity of the general formula I, in which R represents a lipophilic acyl radical containing 23 to 70 carbon atoms that can be linear or branched or cyclic or polycyclic. The lipophilic analog of N-acetylnormuramoyl-L-{alpha}-aminobutanoyl-D-isoglutamine of the general formula I is prepared in such a manner that benzyl-2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-methoxycarbonylmethyl-{alpha}-D-glucopyranoside of the general formula II is condensed after saponification to benzyl-2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-carboxymethyl-{alpha}-D-glucopyranoside of the general formula III with a peptide component to give the substance of the general formula IV, whereupon the substance of the general formula IV is converted by cleaving the isopropylidene group to benzyl ester of N-(2-O-(benzyl 2-acetamido-2,3-dideoxy-{alpha}D-glucopyranosid-3-yl)-glycoloyl)-L-{alpha}-aminobutanoyl-D-isoglutamine of the general formula V, which is then partially acylated to give 6-O-acyl benzyl ester derivatives of N-(2-O-(benzyl-2-acetamido-2,3-dideoxy-{alpha}-D-glucopyranosid-3-yl)-glycoloyl)-L-{alpha}-aminobutanoyl-D-isoglutamine of the general formula VI. Subsequently, cleavage of benzyl protecting groups from the substances of the general formulae V and VI takes place by hydrogenolysis to give N-acetyl-normuramoyl-L-{alpha}-aminobutanoyl-D-isoglutamine of the general formula I', in which R represents a hydrogen atom and 6-O-acyl derivatives of the general formula I thereof, wherein R represents a lipophilic acyl radical having 23 to 70 carbon atoms that is either linear or branched or cyclic or polycyclic.